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Published TCIMAIL newest issue No.199
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CAS RN: 12148-71-9 | Produkte #: C2662
(1,5-Cyclooctadiene)(methoxy)iridium(I) Dimer
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Reinheit:
Synonyme
- Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I)
Produktdokumente:
| Einheit | Stückpreis | Belgien | Japan* | Menge |
|---|---|---|---|---|
| 200MG |
€123.00
|
15 | ≥100 |
|
| 1G |
€609.00
|
1 | ≥100 |
|
*In Belgien verfügbare Lagerbestände werden in 1 bis 3 Tagen geliefert.
*In Japan verfügbare Lagerbestände werden in 1 bis 2 Wochen geliefert. (unter Ausschluss von regulierten Artikeln und Trockeneislieferungen).
| Artikel # | C2662 |
| Summenformel / Molekülmasse | C__1__8H__3__0Ir__2O__2 = 662.87 |
| Physikalischer Zustand (20 °C) | Solid |
Lagerungstemperatur 
|
Frozen (<0°C) |
| Unter Inertgas lagern | Store under inert gas |
| Zu vermeidende Bedingungen | Light Sensitive,Air Sensitive,Moisture Sensitive,Heat Sensitive |
| Verpackung und Behälter
|
1G-Glass Bottle with Plastic Insert (Bild ansehen), 200MG-Glass Bottle with Plastic Insert (Bild ansehen) |
| CAS RN | 12148-71-9 |
| Reaxys Registrierungsnummer | 14520157 |
| PubChem-Stoff-ID | 160871404 |
| MDL-Nummer | MFCD08459360 |
Spezifikation
| Appearance | Light yellow to Amber to Dark green powder to crystal |
| Elemental analysis(Carbon) | 31.50 to 34.00 % |
Eigenschaften
| Schmelzpunkt | 179 °C(dec.) |
GHS
Verwandte Gesetze:
Transportinformationen:
| HS-Nr. (Import / Export) (TCI-E) | 2843909000 |
Anwendung
TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst
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Used Chemicals
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Procedure
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A solution of dtbpy (27 mg, 0.05 mmol), bis(pinacolato)diboron (1.0 g, 4.0 mmol) and [Ir(cod)OMe]2 (33 mg, 0.025 mmol) in cyclohexane (40 mL) was stirred under nitrogen at room temperature for 10 min. Benzo[1,2-b:4,5-b']dithiophene (380 mg, 2.0 mmol) was added the mixture and stirred 80 ˚C for 18 hours. The reaction mixture was quenched with water and separated both layers, extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was washed with methanol (20 mL) to give 1 as a white solid (0.771 g, 87% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by NMR.
Cyclohexane was bubbled with nitrogen before use.
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Analytical Data
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Compound 1
1H NMR (270 MHz, CDCl3); δ 8.36 (s, 2H), 7.90 (s, 2H), 1.39 (s, 24H).
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Lead Reference
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- Synthesis and Transistor Application of Bis[1]benzothieno[6,7‑d:6′,7′‑d′]benzo[1,2‑b:4,5‑b′]dithiophenes
Anwendung
Hartwig-Miyaura C-H Borylation
Reference
- Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent
Anwendung
Catalytic Functionalization of Un-activated Primary C―H Bonds
Typical Procedure:
An alcohol or ketone substrate is dissolved in THF and treated with a freshly prepared solution of [Ir(cod)OMe]2 (0.05 mol%) in THF and then with neat Et2SiH2 (1.2 eq.). The resulting solution is stirred at room temperature (23 °C) until complete conversion of the alcohol or ketone. At the completion of the reaction, the corresponding diethyl(hydrido)silyl ether is observed. Then the reaction mixture is placed under high vacuum for 1 h. The concentrated diethyl(hydrido)silyl ether is sequentially treated with freshly prepared solutions of norbornene (1.2 eq.) in THF and [Ir(cod)OMe]2 (0.5 mol%) in THF, and then with a slurry of Me4phen (1.25 mol%) in THF. The resulting solution is stirred at room temperature for 1 h and then heated it at 80-120 °C until complete conversion to the corresponding oxasilolane is observed. Then the crude reaction mixture containing the oxasilolane is sequentially treated with MeOH, KHCO3 (2.5 eq.) and H2O2 (30% solution in H2O, 10 eq.), and the resulting mixture is stirred overnight at 50 °C. The reaction is carefully quenched with aq. NaHSO3, and the resulting mixture is extracted with EtOAc. The combined organic layer is sequentially washed with 1 M HCl and sat. NaHCO3, and then dried with MgSO4. The resulting organic layer is filtered through Celite and concentrated to provide the crude diol, which is either purified directly or after conversion to the corresponding acetate derivative through treatment with Ac2O and Et3N.
An alcohol or ketone substrate is dissolved in THF and treated with a freshly prepared solution of [Ir(cod)OMe]2 (0.05 mol%) in THF and then with neat Et2SiH2 (1.2 eq.). The resulting solution is stirred at room temperature (23 °C) until complete conversion of the alcohol or ketone. At the completion of the reaction, the corresponding diethyl(hydrido)silyl ether is observed. Then the reaction mixture is placed under high vacuum for 1 h. The concentrated diethyl(hydrido)silyl ether is sequentially treated with freshly prepared solutions of norbornene (1.2 eq.) in THF and [Ir(cod)OMe]2 (0.5 mol%) in THF, and then with a slurry of Me4phen (1.25 mol%) in THF. The resulting solution is stirred at room temperature for 1 h and then heated it at 80-120 °C until complete conversion to the corresponding oxasilolane is observed. Then the crude reaction mixture containing the oxasilolane is sequentially treated with MeOH, KHCO3 (2.5 eq.) and H2O2 (30% solution in H2O, 10 eq.), and the resulting mixture is stirred overnight at 50 °C. The reaction is carefully quenched with aq. NaHSO3, and the resulting mixture is extracted with EtOAc. The combined organic layer is sequentially washed with 1 M HCl and sat. NaHCO3, and then dried with MgSO4. The resulting organic layer is filtered through Celite and concentrated to provide the crude diol, which is either purified directly or after conversion to the corresponding acetate derivative through treatment with Ac2O and Et3N.
References
PubMed Literatur
Dokumente
Produktartikel
[TCI Practical Example] Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst[Research Articles] Catalytic Functionalization of Un-activated Primary C-H Bonds
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